N-(2-Hydroxyethyl)oleamid

Oleoylethanolamide

HCID 5283454
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Grundinformationen

CAS
111-58-0
Standard-SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCO
InChIKey
BOWVQLFMWHZBEF-KTKRTIGZSA-N
Summenformel
C20H39NO2
Durchschnittliche Molmasse
325,5 g/mol
Monoisotopische Masse
325,29807949

Überblick

Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a geroprotector, a PPARalpha agonist and an EC 3.5.1.23 (ceramidase) inhibitor. It is a N-acylethanolamine 18:1, a N-(long-chain-acyl)ethanolamine and an endocannabinoid. It is functionally related to an oleic acid.

Namen und Bezeichner

Bevorzugter Name
Oleoylethanolamide
IUPAC
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
Lokaler Name
N-(2-Hydroxyethyl)oleamid
Englischer Name
Oleoyl Ethanolamide
Summenformel
C20H39NO2
Molmasse
325.53

Namen und Synonyme

oleoylethanolamide111-58-0N-(2-Hydroxyethyl)oleamideOleoyl Ethanolamide(Z)-N-(2-hydroxyethyl)octadec-9-enamideOleoyl monoethanolamideOLEIC MONOETHANOLAMIDEN-(9Z-octadecenoyl)-ethanolamine1HI5J9N8E69-Octadecenamide, N-(2-hydroxyethyl)-DTXSID1044516N-(cis-9-octadecenoyl) ethanolamine
Weitere Namen anzeigen
ODAOEAOleoylethanolamide(OEA)OLEAMIDE MEAN-(Hydroxyethyl)oleamideAM-3101UNII-1HI5J9N8E6
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-CHEBI:71466RefChem:856533DTXCID9024516203-884-8Oleoylethanolaminen-oleoylethanolamineOleylethanolamide

Datenbank-Bezeichner

CAS
111-58-0
PubChem CID
5283454
DTXSID
DTXSID1044516
ChEMBL
CHEMBL280065
ChEBI
CHEBI:71466
UNII
1HI5J9N8E6
EC Number
203-884-8、921-073-3
Nikkaji
J193.596H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
49,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
17
Schwere Atome
23

Experimentelle und physikochemische Eigenschaften

LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Cosmetics · 3 Einträge

Cosmetic ingredients (Oleamide MEA) -> CIR (Cosmetic Ingredient Review)

Personal care product

Antistatic; Viscosity controlling; Foam boosting

Physical Description · 2 Einträge

Other Solid

Solid

Collision Cross Section192.94 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

Physikochemische Eigenschaften

Schmelzpunkt
63 · 63-64 °C
Siedepunkt
496.4 · 496.4±38.0 °C(Predicted)
Dichte
0.915 · 0.915±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 35 mg/ml)
Aggregatzustand
White solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 205 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19715

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxikologische Informationen

Toxicity Summary · 2 Einträge

The CIR Expert Panel concluded that the ethanolamides listed subsequently are safe in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating. The Expert Panel cautioned that these ingredients should not be used in cosmetic products in which N-nitroso compounds may be formed...Oleamide MEA...

Safe for use in cosmetics, with qualifications

Sicherheitsdaten

wgk
2
tsca
TSCA listed
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36
hazard_class
IRRITANT

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor-α (PPAR-α) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.

Tissue LocationsPlacenta
Cellular LocationsExtracellular

Verwendung und Herstellung

UsesCIR ingredient: Oleamide MEA
U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesSurfactant (surface active agent)
Industry UsesSurfactant (surface active agent)
Use ClassificationCosmetics -> Antistatic; Viscosity controlling; Foam boosting
General Manufacturing Information · 2 Einträge

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: ACTIVE

Anwendungen · 2 Einträge

BeschreibungOleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

VerwendenN-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
山东天微医药科技有限公司+86-18653895227 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海毕合生物化学技术有限公司13816464724 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a PPARalpha agonist, an EC 3.5.1.23 (ceramidase) inhibitor and a geroprotector. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-acylethanolamine 18:1. It is functionally related to an oleic acid.

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